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Record Information
Version3.6
Creation Date2009-04-06 16:21:04 UTC
Update Date2016-02-11 01:23:52 UTC
HMDB IDHMDB12210
Secondary Accession NumbersNone
Metabolite Identification
Common NameDihydrolipoate
DescriptionDihydrolipoic acid is an organic compound that is the reduced form of lipoic acid. This carboxylic acid features a pair of thiol groups. It is optically active but only the R-enantiomer is biochemically significant. The lipoic acid/dihydrolipoic acid pair participate in a variety of biochemical transformations.( from Wiki). Inside the cell, alpha lipoic acid is readily reduced or broken down to dihydrolipoic acid. Dihydrolipoic acid is even more potent than alpha lipoic acid, neutralizing free radicals, preventing them from causing harm. It directly destroys damaging superoxide radicals, hydroperoxy radicals and hydroxyl radicals. It has been shown in vitro that dihydrolipoate (DL-6,8-dithioloctanoic acid) has antioxidant activity against microsomal lipid peroxidation.Dihydrolipoate is tested for its neuroprotective activity using models of hypoxic and excitotoxic neuronal damage in vitro and rodent models of cerebral ischemia in vivo. Dihydrolipoate, similarly to dimethylthiourea, is able to protect neurons against ischemic damage by diminishing the accumulation of reactive oxygen species within the cerebral tissue.(PMID: 1345759 ).
Structure
Thumb
Synonyms
ValueSource
6,8-Bis-sulfanyloctanoic acidChEBI
6,8-Dihydrothioctic acidChEBI
6,8-dimercapto-Octanoic acidChEBI
6,8-Dimercaptooctanoic acidChEBI
DHLAChEBI
dihydro-alpha-Lipoic acidChEBI
dihydro-Lipoic acidChEBI
Dihydrothioctic acidChEBI
6,8-Bis-sulfanyloctanoateGenerator
6,8-Bis-sulphanyloctanoateGenerator
6,8-Bis-sulphanyloctanoic acidGenerator
Dihydrolipoic acidGenerator
6,8-DihydrothioctateGenerator
6,8-dimercapto-OctanoateGenerator
6,8-DimercaptooctanoateGenerator
dihydro-a-LipoateGenerator
dihydro-a-Lipoic acidGenerator
dihydro-alpha-LipoateGenerator
dihydro-α-lipoateGenerator
dihydro-α-lipoic acidGenerator
dihydro-LipoateGenerator
DihydrothioctateGenerator
6,8-DisulfanyloctanoateHMDB
6,8-Disulfanyloctanoic acidHMDB
D,L-DihydrolipoateHMDB
D,L-Dihydrolipoic acidHMDB
dihydro-DL-alpha-LipoateHMDB
dihydro-DL-alpha-Lipoic acidHMDB
dihydro-Thioctic acidHMDB
dihydro-Thiocytic acidHMDB
DL-dihydro-a-6-Thioctic acidHMDB
DL-dihydro-alpha-6-Thioctic acidHMDB
Reduced DL-6,8-thioctic acidHMDB
Reduced lipoateHMDB
Reduced lipoic acidHMDB
Reduced thioctic acidHMDB
Chemical FormulaC8H16O2S2
Average Molecular Weight208.341
Monoisotopic Molecular Weight208.059171136
IUPAC Name6,8-disulfanyloctanoic acid
Traditional Namedihydrolipoic acid
CAS Registry Number462-20-4
SMILES
OC(=O)CCCCC(S)CCS
InChI Identifier
InChI=1S/C8H16O2S2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H,9,10)
InChI KeyInChIKey=IZFHEQBZOYJLPK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Thia fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 mg/mLALOGPS
logP2.24ALOGPS
logP2.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)4.91ChemAxon
pKa (Strongest Basic)-9.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity55.94 m3·mol-1ChemAxon
Polarizability23.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
3-Phosphoglycerate dehydrogenase deficiencySMP00721Not Available
Ammonia RecyclingSMP00009map00910
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)SMP00179Not Available
Dimethylglycine Dehydrogenase DeficiencySMP00242Not Available
Dimethylglycine Dehydrogenase DeficiencySMP00484Not Available
Glycine and Serine MetabolismSMP00004map00260
Hyperglycinemia, non-ketoticSMP00485Not Available
Non Ketotic HyperglycinemiaSMP00223Not Available
SarcosinemiaSMP00244Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028855
KNApSAcK IDNot Available
Chemspider ID408
KEGG Compound IDC02147
BioCyc ID6-S-ACETYL-DIHYDROLIPOATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12210
Metagene LinkHMDB12210
METLIN IDNot Available
PubChem Compound421
PDB IDNot Available
ChEBI ID18047
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Prehn JH, Karkoutly C, Nuglisch J, Peruche B, Krieglstein J: Dihydrolipoate reduces neuronal injury after cerebral ischemia. J Cereb Blood Flow Metab. 1992 Jan;12(1):78-87. [1345759 ]